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How to Talk to Your Parents About Their Estate Plans Without It Being Awkward

Talking about money can be a recipe for tension and miscommunication among family members. Bring in retirement and estate planning—and your aging parents—and you’ve concocted a conversation no one really wants to have. I’ve previously covered how aging parents can broach this subject with their adult children, but what about the reverse? How can adult children talk to their parents about their retirement, estate, and other long-term financial plans?

Discussing retirement plans with your aging parents can be difficult, but it’s a necessary conversation to have. As your parents get older, they will need support and assistance in planning out their golden years. I spoke with Mitch Mitchell, associate counsel at Trust & Will, for tips to guide this crucial financial conversation with your parents. 

Pick a Good Time

Choose a time when you and your parents are both relaxed and not rushed or stressed. Avoid bringing up the topic of retirement during big family gatherings or holidays. Instead, set aside a separate time just for this discussion.


Come Prepared

Before the conversation, take some time to think about what questions you want to ask. Jot down topics like living arrangements, finances, healthcare, estate planning, social activities, etc. This will help the discussion stay focused and productive.


If you’re (understandably) struggling to find the right words, Mitchell offers this sample script: “Look, Mom/Dad. I want to honor your wishes. But I can’t do that if I don’t know your wishes.” The key is framing the conversation around their wants and needs, not any selfish motive on your part.


Listen More Than Talk

As Mitchell puts it, there are two roadblocks here: One is our societal reservations about money talk in general; the second is our reluctance to think about us or our loved ones dying.


Go into the conversation with an open mind. Let your parents share their thoughts and wishes before imposing your own opinions. Active listening is key here. Avoid dismissing or arguing with their plans right away.


Discuss Their Goals

Ask what your parents envision for their retirement years. Do they have dreams of traveling or spending time with grandchildren? Get a sense of how they want to spend their time and what brings them joy. This will provide insight into the type of living and financial arrangements that suit them best.


Address Any Concerns

Mitchell says to voice worries you may have about their health and wellbeing in a caring, non-judgmental way. Your role is to kindly share potential issues, not dictate what they should do. Aging parents may need a little push to address things like declining health, isolation, or financial problems.


To break the ice, Mitchell offers another tip: Talk about your own family planning first. Especially if you have young kids yourself, open up to your parents about how uncomfortable it was to think about your own end-of-life wishes. Uncomfortable, but necessary—and that you’re glad you did.


Present Options

Suggest options like moving closer to family, downsizing to a smaller home, participating in senior activities, or meeting with a financial advisor. Provide resources without insisting they take your advice. Guide them compassionately toward wise choices.


Make Follow-Up Plans

Mitchell advises that this will be more than one conversation. Schedule regular check-ins to continue the retirement conversation. Chat about any updates to their plans or needs. Make yourself available as a resource and supportive advocate. With ongoing cooperation, you can help your parents have a comfortable and enjoyable retirement.

Discussing your aging parents’ retirement plans may feel awkward, but it’s a wise and caring move for everyone involved. Keep communication open as their needs and desires evolve. With patience and compassion, you can have productive talks to ensure their golden years are truly happy ones.



For more tips on all kinds of estate-planning topics, check out Trust & Will’s resources here.



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Renee E. Nesbit, Attorney at Law

1415 Panther Lane, Suite 434
Naples FL 34109

The information contained on this website is presented for informational and marketing purposes only and is not to be understood as legal advice. You should consult an attorney for advice respecting your individual needs. Renee E. Nesbit, Attorney at Law looks forward to speaking with you about your particular needs. Please note, however, that the mere act of contacting our firm does not create an attorney-client relationship. As a result, you should never send any confidential information to our office until a Representation Agreement has been signed by both you and Renee E. Nesbit, Attorney at Law.

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